1. Field of the Invention
The invention is related to a catalytic method for the production of N-substituted (meth)acrylamides and is more particularly related to a catalytic method for the production of N-substituted (meth)acrylamides from (meth)acrylates and amines in the presence of an alkoxide of silicon, titanium or zirconium.
2. Prior Art
U.S. Pat. No. 4,206,143 (corresponding to British patent application No. 2,021,101A) reveals that dialkyl stannic oxide catalysts, such as dibutyl stannic oxide, are effective for the preparation of N-substituted acrylamides and methacrylamides from the reaction of an alkyl ester of acrylic or methacrylic acid with an aliphatic, cycloaliphatic or aromatic amine, which is a primary or secondary amine.
U.S. Pat. No. 4,321,411, issued on Mar. 23, 1982, relates to a process for producing an N-substituted acrylamide or methacrylamide comprising reacting an acrylic or methacrylic acid ester with an aliphatic or aromatic amine in a liquid medium in the presence of a catalytic amount of an alkyltin alkoxide such as dibutyl dimethoxytin. This patent corresponds to British patent application No. 2,075,495A and Japanese Kokai No. 81-100,749.
Tin compounds are particularly useful as catalysts for the production of dialkylaminoethyl methacrylate. For example, Japanese Kokai No. 76-71,010 (CA 88:121898z) teaches that dialkyltin maleate, dialkyltin mercaptide and dialkylstannanediols are useful catalysts in this regard. Dibutyltin dimethoxide was found to be effective for the catalytic synthesis of dimethylaminoethyl methacrylate (DMAEMA), as described in Japanese Kokai No. 77-153,912 (CA 88:137169y). Further, compounds such as (C.sub.4 H.sub.9).sub.2 Sn(O.sub.2 CR).sub.2, where R is methyl or lauryl, are catalysts for the production of dialkylaminoethyl acrylates and methacrylates, as taught in Japanese Kokai No. 78-34,714 (CA 89:44410a).
U.S. Pat. No. 4,301,297 reveals that DMAEMA may be prepared in high yield by subjecting methyl methacrylate and dimethylaminoethanol to transesterification in the presence of di-n-octyl tin oxide as a catalyst. Compounds such as (C.sub.4 H.sub.9).sub.2 SnR.sub.2 (where R.sub.2 is hydrogen or --OCH.sub.3 or O.sub.2 CCH.dbd.CHCO.sub.2), (n--C.sub.8 H.sub.17).sub.2 SnO, (C.sub.6 H.sub.5).sub.3 SnOCH.sub.3 or (C.sub.4 H.sub.9).sub.3 SnO.sub.2 CCH.dbd.CHC--O.sub.2 Sn(C.sub.4 H.sub.9).sub.3 are effective in the manufacture of dialkylaminoethyl acrylates as seen in Japanese Kokai No. 78-144,522 (CA 90:169290p). In addition, U.S. Pat. No. 4,281,175 discloses that DMAEMA may be made via a number of tin catalysts such as tetrabutyltin, trioctyltin ethoxide, dibutyltin dimethoxide, dibutyltin dihydride, dibutyltin dilaurate, dibutyltin maleate, bis(tributyltin)oxide and bis(dibutylmethoxytin)oxide. See also Poller, R. C., et at., "Organotin Compounds as Transesterification Catalysts", Journal of Organometallic Chemistry, 173(1979) pp. C7-C8.
The above mentioned related patent applications cross-referenced at the beginning of this specification are also relevant in respect of the prior art.